Was life at any point in our past free?

I don't think so.

And if you go back to caveman times before money, we still paid with blood.

If anything life is moving into a situation where it might actually be free. But that does not mean freedom.

We were actually more free in caveman times.

Its a paradox. The more comfortable we get, the more safe we get, and the less we have to pay for this, in the end we will pay with less freedom.